Reaction of (R)-2-butanol with p-toluenesulph | vedclass

Name: Exam Paper Generator | JEE NEET Paper Generator | Vedclass
Brand: Vedclass
Rating: 5 (35 reviews)

Question

(D) The reaction proceeds in two steps:$1$. The reaction of $(R)-2$-butanol with $p$-toluenesulphonyl chloride $(TsCl)$ in pyridine converts the hydro

Vedclass · Accepted Answer

$(S)-2$-butyl bromide

Vedclass · Answer

(D) The reaction proceeds in two steps:$1$. The reaction of $(R)-2$-butanol with $p$-toluenesulphonyl chloride $(TsCl)$ in pyridine converts the hydroxyl group into a good leaving group,the tosylate group $(-OTs)$. This reaction occurs without breaking the $C-O$ bond,so the configuration at the chiral center remains unchanged,resulting in $(R)-2$-butyl tosylate.$2$. The subsequent reaction with $LiBr$ involves a nucleophilic substitution $(S_N2)$ reaction. The bromide ion $(Br^-)$ attacks the chiral carbon from the side opposite to the tosylate group,leading to an inversion of configuration (Walden inversion). Thus,$(R)-2$-butyl tosylate is converted into $(S)-2$-butyl bromide.

Reaction of $(R)-2$-butanol with $p$-toluenesulphonyl chloride in pyridine followed by reaction with $LiBr$ gives

Similar Questions

Which of the following compounds has the highest boiling point?

What is the product formed by the reaction of $HBr$ with $CH_2=CH-OCH_3$ under anhydrous conditions at room temperature?

Vicinal and geminal dihalides can be distinguished by using:

Which one among the following undergoes dehydrohalogenation most readily?

Identify the major product for the following reaction:
$1$-fluoro-$1$-methylcyclohexane $\xrightarrow[\Delta]{Alc. KOH}$ ?

Vedclass Test Series

Exam Paper Generator

Online Exam Module